Direct Detection of the Photorearrangement Reaction of Quinoline-Protected Dialkylanilines.

ABSTRACT: The photolysis reactions of (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ)-caged amines have been investigated using time-resolved spectroscopy methods. Unexpectedly, an unconventional Hofmann-Martius rearrangement reaction with high yield and regioselectivity occurred during the photolysis of some CyHQ-protected dialkylanilines (such as compounds 1a and 2a). To have more insights into the mechanism of this unexpected photorearrangement reaction, we characterized the reaction intermediates directly using time-resolved spectroscopy. Our new results showed that the anionic form of compound 1a was photoexcited to the singlet excited state, then a heterolytic cleavage of the C-N bond took place to give CyHQ⁺ and the corresponding aniline. Thereafter, the recombined intermediate 6 was

SUBMITTER: Liang R 

PROVIDER: S-EPMC9300182 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature